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Search resultsOver 1,000 homes in Avalon Shores, Shady Side

Home in Shady Side
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
3 beds
Mar 20 – 25
$249 per night
Superhost
Home in Shady Side
Cozy 2 bedroom & den
2 beds
Apr 2 – 7
$71 per night, originally $92
Guest suite in Deale
*Chesapeake Bayside Loft*
1 bed
Mar 20 – 25
$74 per night
Home in West River
Cozy waterview home in West River!
3 beds
Apr 2 – 7
$169 per night
Superhost
Cottage in Shady Side
Tranquil West River Retreat - 50 minutes to DC
3 beds
Apr 2 – 7
$220 per night, originally $275
Home in Shady Side
"Pier Envy!" Bayside escape - water & beach views
5 beds
Mar 26 – 31
$264 per night
Superhost
Guesthouse in Galesville
Gorgeous water view studio!
1 queen bed
Mar 20 – 27
$148 per night, originally $165
Superhost
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
3 beds
Apr 15 – 22
$494 per night, originally $581
Superhost
Home in Shady Side
Beautiful Waterfront Community Getaway by the Bay
5 beds
Mar 23 – 28
$265 per night
Bungalow in Deale
Cozy waterfront getaway on the Bay
2 queen beds
May 7 – 12
$143 per night
Superhost
Home in Shady Side
Waterfront Sanctuary only 50 Min. From DC/Balt.
12 beds
Apr 10 – 15
$600 per night
Superhost
Home in Shady Side
Cozy Bay home w/180 degree view
3 beds
Mar 20 – 25
$136 per night, originally $170
Cottage in Shady Side
Chesapeake Cabin
7 beds
Mar 20 – 25
$191 per night, originally $265
Guest suite in Huntingtown
Full Basement In-Law Apartment
1 queen bed
Mar 20 – 25
$67 per night
Superhost
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
Mar 26 – 31
$125 per night
Tiny home in Annapolis
"The Perch" - Tiny 1BR Cottage - Chesapeake Bay
1 queen bed
Mar 21 – 26
$221 per night, originally $245
Superhost
Cottage in Edgewater
Charming water access cottage for you and your dog
2 queen beds
Mar 27 – Apr 1
$138 per night
Superhost
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
1 queen bed
Apr 9 – 14
$80 per night
Superhost